JPS6330524A - メチレン−ビス−ナフタレン化合物を含有する分枝状ポリカ−ボネ−ト及びその製法 - Google Patents
メチレン−ビス−ナフタレン化合物を含有する分枝状ポリカ−ボネ−ト及びその製法Info
- Publication number
- JPS6330524A JPS6330524A JP62182438A JP18243887A JPS6330524A JP S6330524 A JPS6330524 A JP S6330524A JP 62182438 A JP62182438 A JP 62182438A JP 18243887 A JP18243887 A JP 18243887A JP S6330524 A JPS6330524 A JP S6330524A
- Authority
- JP
- Japan
- Prior art keywords
- bis
- methylene
- formula
- naphthalene
- hydroxy
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 239000004417 polycarbonate Substances 0.000 title claims description 42
- 229920000515 polycarbonate Polymers 0.000 title claims description 42
- -1 methylene-bis-naphthalene compound Chemical class 0.000 title claims description 11
- 238000004519 manufacturing process Methods 0.000 title claims description 10
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 claims description 21
- 150000001875 compounds Chemical class 0.000 claims description 17
- 125000003118 aryl group Chemical group 0.000 claims description 16
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 16
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 238000000034 method Methods 0.000 claims description 12
- 238000000071 blow moulding Methods 0.000 claims description 11
- 229920000642 polymer Polymers 0.000 claims description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 9
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 claims description 6
- 239000003960 organic solvent Substances 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- QHPQWRBYOIRBIT-UHFFFAOYSA-N 4-tert-butylphenol Chemical compound CC(C)(C)C1=CC=C(O)C=C1 QHPQWRBYOIRBIT-UHFFFAOYSA-N 0.000 claims description 3
- 229910052799 carbon Inorganic materials 0.000 claims description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims description 3
- 238000000465 moulding Methods 0.000 claims description 3
- 239000011541 reaction mixture Substances 0.000 claims description 3
- ODJUOZPKKHIEOZ-UHFFFAOYSA-N 4-[2-(4-hydroxy-3,5-dimethylphenyl)propan-2-yl]-2,6-dimethylphenol Chemical compound CC1=C(O)C(C)=CC(C(C)(C)C=2C=C(C)C(O)=C(C)C=2)=C1 ODJUOZPKKHIEOZ-UHFFFAOYSA-N 0.000 claims description 2
- 125000000217 alkyl group Chemical group 0.000 claims description 2
- 125000004432 carbon atom Chemical group C* 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 229910052736 halogen Inorganic materials 0.000 claims description 2
- 150000002367 halogens Chemical class 0.000 claims description 2
- 229910052739 hydrogen Inorganic materials 0.000 claims description 2
- 239000003444 phase transfer catalyst Substances 0.000 claims description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 3
- 239000000126 substance Substances 0.000 claims 3
- YQUQWHNMBPIWGK-UHFFFAOYSA-N 4-isopropylphenol Chemical compound CC(C)C1=CC=C(O)C=C1 YQUQWHNMBPIWGK-UHFFFAOYSA-N 0.000 claims 2
- UFWIBTONFRDIAS-UHFFFAOYSA-N Naphthalene Chemical compound C1=CC=CC2=CC=CC=C21 UFWIBTONFRDIAS-UHFFFAOYSA-N 0.000 claims 2
- 125000005587 carbonate group Chemical group 0.000 claims 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 claims 2
- WLJNZVDCPSBLRP-UHFFFAOYSA-N pamoic acid Chemical compound C1=CC=C2C(CC=3C4=CC=CC=C4C=C(C=3O)C(=O)O)=C(O)C(C(O)=O)=CC2=C1 WLJNZVDCPSBLRP-UHFFFAOYSA-N 0.000 claims 2
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 claims 1
- KYPYTERUKNKOLP-UHFFFAOYSA-N Tetrachlorobisphenol A Chemical compound C=1C(Cl)=C(O)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(O)C(Cl)=C1 KYPYTERUKNKOLP-UHFFFAOYSA-N 0.000 claims 1
- VCCBEIPGXKNHFW-UHFFFAOYSA-N biphenyl-4,4'-diol Chemical group C1=CC(O)=CC=C1C1=CC=C(O)C=C1 VCCBEIPGXKNHFW-UHFFFAOYSA-N 0.000 claims 1
- 238000006068 polycondensation reaction Methods 0.000 claims 1
- 125000001302 tertiary amino group Chemical group 0.000 claims 1
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 21
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 12
- 230000035945 sensitivity Effects 0.000 description 9
- 239000007864 aqueous solution Substances 0.000 description 8
- 239000000047 product Substances 0.000 description 7
- 238000001125 extrusion Methods 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000000155 melt Substances 0.000 description 4
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 239000012074 organic phase Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- 229920001169 thermoplastic Polymers 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- 239000012670 alkaline solution Substances 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000003638 chemical reducing agent Substances 0.000 description 2
- 238000007334 copolymerization reaction Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 230000007935 neutral effect Effects 0.000 description 2
- 239000012299 nitrogen atmosphere Substances 0.000 description 2
- 239000012071 phase Substances 0.000 description 2
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
- JVBXVOWTABLYPX-UHFFFAOYSA-L sodium dithionite Chemical compound [Na+].[Na+].[O-]S(=O)S([O-])=O JVBXVOWTABLYPX-UHFFFAOYSA-L 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000004416 thermosoftening plastic Substances 0.000 description 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 description 2
- ZMESHQOXZMOOQQ-UHFFFAOYSA-N 1-(naphthalen-1-ylmethyl)naphthalene Chemical class C1=CC=C2C(CC=3C4=CC=CC=C4C=CC=3)=CC=CC2=C1 ZMESHQOXZMOOQQ-UHFFFAOYSA-N 0.000 description 1
- DBRZAWITJCPDAD-UHFFFAOYSA-N 2h-naphthalen-1-ylidenemethanone Chemical compound C1=CC=C2C(=C=O)CC=CC2=C1 DBRZAWITJCPDAD-UHFFFAOYSA-N 0.000 description 1
- ALKYHXVLJMQRLQ-UHFFFAOYSA-N 3-Hydroxy-2-naphthoate Chemical compound C1=CC=C2C=C(O)C(C(=O)O)=CC2=C1 ALKYHXVLJMQRLQ-UHFFFAOYSA-N 0.000 description 1
- RLCZBUOZNFAZLK-UHFFFAOYSA-N 3-hydroxynaphthalene-2-carbonyl chloride Chemical compound C1=CC=C2C=C(C(Cl)=O)C(O)=CC2=C1 RLCZBUOZNFAZLK-UHFFFAOYSA-N 0.000 description 1
- 229930185605 Bisphenol Natural products 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 230000002730 additional effect Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000006085 branching agent Substances 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 238000004581 coalescence Methods 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 230000008034 disappearance Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 238000010406 interfacial reaction Methods 0.000 description 1
- NSNPSJGHTQIXDO-UHFFFAOYSA-N naphthalene-1-carbonyl chloride Chemical compound C1=CC=C2C(C(=O)Cl)=CC=CC2=C1 NSNPSJGHTQIXDO-UHFFFAOYSA-N 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- UHZYTMXLRWXGPK-UHFFFAOYSA-N phosphorus pentachloride Chemical compound ClP(Cl)(Cl)(Cl)Cl UHZYTMXLRWXGPK-UHFFFAOYSA-N 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 230000001376 precipitating effect Effects 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000004611 spectroscopical analysis Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G64/00—Macromolecular compounds obtained by reactions forming a carbonic ester link in the main chain of the macromolecule
- C08G64/04—Aromatic polycarbonates
- C08G64/06—Aromatic polycarbonates not containing aliphatic unsaturation
- C08G64/14—Aromatic polycarbonates not containing aliphatic unsaturation containing a chain-terminating or -crosslinking agent
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyesters Or Polycarbonates (AREA)
- Indole Compounds (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Medicinal Preparation (AREA)
- Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IT21233A/86 | 1986-07-23 | ||
| IT21233/86A IT1196988B (it) | 1986-07-23 | 1986-07-23 | Policarbonati ramificati contenenti composti metilen-bis-naftalenici e procedimento per la loro preparazione |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS6330524A true JPS6330524A (ja) | 1988-02-09 |
Family
ID=11178784
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP62182438A Pending JPS6330524A (ja) | 1986-07-23 | 1987-07-23 | メチレン−ビス−ナフタレン化合物を含有する分枝状ポリカ−ボネ−ト及びその製法 |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US4798882A (ko) |
| EP (1) | EP0254371B1 (ko) |
| JP (1) | JPS6330524A (ko) |
| AT (1) | ATE72255T1 (ko) |
| CA (1) | CA1285692C (ko) |
| DE (1) | DE3776445D1 (ko) |
| DK (1) | DK379987A (ko) |
| ES (1) | ES2030709T3 (ko) |
| GR (1) | GR3003933T3 (ko) |
| IT (1) | IT1196988B (ko) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0250029U (ko) * | 1988-09-28 | 1990-04-06 | ||
| JPH03163132A (ja) * | 1989-08-03 | 1991-07-15 | Idemitsu Petrochem Co Ltd | 分岐状ポリカーボネート及びその製造法 |
| JPH03163131A (ja) * | 1989-08-03 | 1991-07-15 | Idemitsu Petrochem Co Ltd | 分岐状ポリカーボネート及びその製造方法 |
| JP2014214220A (ja) * | 2013-04-25 | 2014-11-17 | 帝人株式会社 | ポリカーボネート |
Families Citing this family (11)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5693741A (en) | 1988-03-15 | 1997-12-02 | The Boeing Company | Liquid molding compounds |
| US5705598A (en) | 1985-04-23 | 1998-01-06 | The Boeing Company | Polyester sulfone oligomers and blends |
| US5512676A (en) | 1987-09-03 | 1996-04-30 | The Boeing Company | Extended amideimide hub for multidimensional oligomers |
| US5969079A (en) | 1985-09-05 | 1999-10-19 | The Boeing Company | Oligomers with multiple chemically functional end caps |
| US5210213A (en) | 1983-06-17 | 1993-05-11 | The Boeing Company | Dimensional, crosslinkable oligomers |
| US5516876A (en) | 1983-09-27 | 1996-05-14 | The Boeing Company | Polyimide oligomers and blends |
| US5714566A (en) | 1981-11-13 | 1998-02-03 | The Boeing Company | Method for making multiple chemically functional oligomers |
| US5618907A (en) | 1985-04-23 | 1997-04-08 | The Boeing Company | Thallium catalyzed multidimensional ester oligomers |
| US5817744A (en) | 1988-03-14 | 1998-10-06 | The Boeing Company | Phenylethynyl capped imides |
| US5166306A (en) * | 1988-12-02 | 1992-11-24 | Enichem Technoresine S.P.A. | Flame-resistant polycarbonate containing units from halogenated pyrimidine compounds in the polymer chain |
| US5447989A (en) * | 1993-09-17 | 1995-09-05 | Enichem S.P.A. | High impact modified polycarbonate compositions |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3525712A (en) * | 1965-09-01 | 1970-08-25 | Gen Electric | Process for preparing thermoplastic polycarbonates |
| US4562242A (en) * | 1984-12-24 | 1985-12-31 | General Electric Company | Branched polycarbonate from carboxy containing diphenol |
| IT1214645B (it) * | 1985-12-19 | 1990-01-18 | Enichem Polimeri | Policarbonati ramificati contenenti composti aromatici binucleari. |
-
1986
- 1986-07-23 IT IT21233/86A patent/IT1196988B/it active
-
1987
- 1987-07-17 US US07/075,042 patent/US4798882A/en not_active Expired - Fee Related
- 1987-07-17 DE DE8787201368T patent/DE3776445D1/de not_active Expired - Fee Related
- 1987-07-17 EP EP87201368A patent/EP0254371B1/en not_active Expired - Lifetime
- 1987-07-17 ES ES198787201368T patent/ES2030709T3/es not_active Expired - Lifetime
- 1987-07-17 AT AT87201368T patent/ATE72255T1/de not_active IP Right Cessation
- 1987-07-21 DK DK379987A patent/DK379987A/da not_active Application Discontinuation
- 1987-07-22 CA CA000542769A patent/CA1285692C/en not_active Expired - Fee Related
- 1987-07-23 JP JP62182438A patent/JPS6330524A/ja active Pending
-
1992
- 1992-02-28 GR GR920400357T patent/GR3003933T3/el unknown
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0250029U (ko) * | 1988-09-28 | 1990-04-06 | ||
| JPH03163132A (ja) * | 1989-08-03 | 1991-07-15 | Idemitsu Petrochem Co Ltd | 分岐状ポリカーボネート及びその製造法 |
| JPH03163131A (ja) * | 1989-08-03 | 1991-07-15 | Idemitsu Petrochem Co Ltd | 分岐状ポリカーボネート及びその製造方法 |
| JP2014214220A (ja) * | 2013-04-25 | 2014-11-17 | 帝人株式会社 | ポリカーボネート |
Also Published As
| Publication number | Publication date |
|---|---|
| GR3003933T3 (ko) | 1993-03-16 |
| ES2030709T3 (es) | 1992-11-16 |
| DK379987D0 (da) | 1987-07-21 |
| DK379987A (da) | 1988-01-24 |
| DE3776445D1 (de) | 1992-03-12 |
| ATE72255T1 (de) | 1992-02-15 |
| IT1196988B (it) | 1988-11-25 |
| US4798882A (en) | 1989-01-17 |
| EP0254371A3 (en) | 1989-05-10 |
| EP0254371A2 (en) | 1988-01-27 |
| EP0254371B1 (en) | 1992-01-29 |
| IT8621233A1 (it) | 1988-01-23 |
| CA1285692C (en) | 1991-07-02 |
| IT8621233A0 (it) | 1986-07-23 |
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